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Remembering the Best Horses That Failed to Win the Triple Crown

| May 4, 2022 10:01 am PDT
Book cover of the Triple Crown, Sir Barton the first Triple Crown winner, and Secretariat

In the hundred-year history of the US Triple Crown—the Kentucky Derby, the Preakness, and the Belmont Stakes, only 13 horses have taken the Triple Crown trophy home.

There have been at least seven more than almost made that list but, for one reason or another, missed capturing the third jewel of the Triple Crown by that much.

As it is said, the race is not always to the swift. Here are the stories of those hapless seven horses—each of which was the fastest horse in the race—until they weren’t.

2004 — Smarty Jones by a Length to Birdstone

The three-year-old chestnut colt Smarty Jones entered the final gem in the Triple Crown undefeated.

From his first maiden attempt to the Kentucky Derby and the Preakness, Smarty Jones denied the winner’s circle to his competitors as though it were his own private paddock.

But something happened at the Belmont Stakes.
Smarty Jones

When the gates banged open, the heavily favored Smarty Jones was among the leaders. And by the mile mark, he was in the lead by a length. But this is the Belmont, at a mile and a half, the longest of the Triple Crown races.

In the Belmont Stakes, the mile mark is just two-thirds of the way to the finish line. Still, Smarty Jones held the lead through most of the final stretch but gave up the lead to 35/1 longshot Birdstone in the last 70 yards.

For his part, Birdstone slowly worked his way from the cheap seats until he was able to challenge Smarty Jones for supremacy that lasted 70 yards.

1998 — Real Quiet by a Nose to Victory Gallop

Real Quiet was the odds-on favorite to win the 1998 Belmont Stakes, and Victory Gallop—the second-favored at 7/2—wasn’t that far behind. And as the race unfolded, it looked like the two would be the first two to hit the wire.

In sixth place right after the break, Real Quiet began easing his way to the front. Meanwhile, Victory Gallop was doing the same thing, sliding from tenth place to fifth place by the 1-1/4 mile mark (at which point Real Quiet had taken the lead).

The two battled down the final stretch, and even as they crossed the wire, it wasn’t clear who had won.

It took the careful examination of the photo-finish to determine that Victory Gallop had won the Belmont Stakes by an actual nod—that head-bobbing a horse does as it runs that on the downstroke puts the horse’s muzzle slightly farther ahead.

This race was easily the closest win and the most heartbreaking of defeats in the history of the Triple Crown.

1997 — Silver Charm by 1-3/4 Lengths to Touch Gold

Silver Charm

At 1/2 odds, Silver Charm was the favorite in one of the smallest fields of Belmont Stakes competitors—seven horses, including the 1/1A coupled entry, Touch Gold, and Wild Rush.

The gray roan colt Silver Charm won the Kentucky Derby by a head, then aced the Preakness the same way—by ahead. The top three finishers in those races were Silver Charm, Captain Bogdet, and Free House, the latter pair trading second and third between the two races.

Touch Gold, who wasn’t in the Kentucky Derby, finished fourth in the Preakness. Then seized the initiative at the break at the Belmont, holding the lead through the first quarter mile, while Silver Charm languished just ahead of the also-rans.

At the 1-1/4-mile mark, Silver Charm took the lead and dueled with Free House to retain the lead for the next furlong.

In the last few yards, however, Free House dropped to third place while Touch Gold surged into the lead, and when they crossed the wire, Silver Charm was nearly two lengths behind the victorious Touch Gold.

1989 — Sunday Silence Is a Distant Second to Easy Goer

This epic race doesn’t deserve a simple text description because it doesn’t do justice to the nail-biting impact of this upset. Just see for yourself.

Still, for those who prefer their hearts shaken, not stirred, here’s the bar-napkin version.

The 1989 Belmont Stakes wasn’t just the final jewel in the Triple Crown; it was one of the first—and certainly the most talked-about—battles between East Coast thoroughbred royalty and what some considered the West Coast pretenders to the throne.

New York’s Easy Goer represented the East Coast, a three-year-old chestnut colt born in Kentucky but schooled at tracks throughout the East. The West Coast’s champion was Sunday Silence, born in Kentucky but spent his professional life in Southern California.

The rivalry become part of thoroughbred racing’s lore, and Easy Goer’s trainer, Claude R. “Shug”  McGaughey III, said it best.

“It was a lot of fun because it was East Coast vs. West Coast, a young trainer vs. an old trainer, West Coast jockey, East Coast jockey.”

The pair met for the first time at Churchill Downs for the 1989 Kentucky Derby. The race began—and Easy Goer (the favorite) trailed behind Sunday Silence throughout the entire mile and a quarter, managing to narrow the gap as the horses neared the finish line.

Sunday Silence finished the race in the first place, 2-1/2 lengths ahead of Easy Goer, the second-place finisher.

A couple of weeks later, the pair met again at the Preakness Stakes. Despite his loss to Sunday Silence in the Derby, Easy Goes was again favored to win. This race began like the Derby, with Easy Goer chasing after Sunday Silence, but there would be a difference this time.

As the pair entered the final stretch, Sunday Silence took the lead. The two were still fighting for the lead when they hit the wire, and the photo-finish showed that Sunday Silence had beaten Easy Goer again—this time, by a nose.

When they met for the Belmont Stakes on June 10, 1989, Sunday Silence was the favorite to win. The gates banged open, and Easy Goer took an early lead,

Although both horses performed at their optimum, Easy Goer maintained that lead, drawing off as the finish line approached until he crossed the wire a commanding 8-1/2 lengths ahead of Sunday Silence.

Incidentally, the competitors met one more time at the Breeders’ Classic in November 1989. Easy Goer was again the favorite, with Sunday Silence the second-favored.

Both horses were part of the pack chasing the early leaders at the break and through the first part of the race, but Easy Goer made his move in the backstretch.

Serving as a textbook example of “jockeying for position,” Easy Goer caught up with Sunday Silence, and the two battled for the lead. With three furlongs remaining, it looked like Easy Goer would even the score. But despite one final burst of acceleration, Easy Goer could not best his rival, and Sunday Silence won the Breeders’ Cup Classic by a neck.

1969 — Majestic Prince by 5-1/2 Lengths to Arts and Letters

One of few horses in the history of the Kentucky Derby to begin the Triple Crown competition undefeated, the three-year-old chestnut colt Majestic Prince seemed born for greatness. From his $250,000 purchase by Canadian oilman Frank McMahon to his seemingly unstoppable tour of U.S. winner’s circles.

Majestic Prince was the 7/5 favorite when he entered the starting gate at Churchill Downs for the Kentucky Derby, and he justified that faith when he bested Arts and Letters to win the Derby by a neck.

Fun Fact
Majestic Prince’s trainer, Johnny Longden, is the only person in history to have won the Kentucky Derby both as a jockey (Count Fleet, 1943) and as a trainer.

Next up was the Preakness, and again Majestic Prince proved himself a winner, crossing the finish line ahead before Arts and Letters.

But the media’s “The Prince” emerged from the Preakness with a slight check ligament injury, and trainer Johnny Longden told reporters that the colt was not going to compete in the Belmont Stakes but would return to California for some R&R.

What made owner McMahon decide to race Majestic Prince in the Belmont Stakes?

The pressure was on—after all, “The Prince” was a media star, a hero to racing fans. Majestic Prince was well-positioned to become the first horse in 20 years to win the Triple Crown.

Or perhaps McMahon considered the injury minor enough not to matter. There were reports of McMahon and Longden having a “shouting match” at the stables in the days preceding the Belmont Stakes. It’s unlikely the two longtime friends were arguing over where to have lunch.

Whatever the reason, Majestic Prince was in the starting gate at Belmont Park that Saturday afternoon in Elmont, New York. He finished second—five-and-a-half lengths behind Arts and Letters.

Jockey Bill Hartack said that “the horse was hurting during the race.” Trainer Longden told reporters bluntly, “We never should have run him in the Belmont.” And despite Longden’s attempts to race Majestic Prince in the following months, “The Prince” would never race again.

1958 — Tim Tam by Six Lengths to Cavan

Tim Tam

Tim Tam started his career in 1957 when he turned in an unimpressive also-ran performance for his first professional race. However, he was a different horse when 1958 rolled around, and he won five major stakes races before entering the starting gates for both the Kentucky Derby and the Preakness.

From the break at the Belmont Stakes, Cavan and Tim Tam hung back, trailing the leaders as they fought a battle between themselves. Cavan managed to stay just ahead of  Tim Tam.

Cavan’s owner, Joseph E. O’Connell, later told reporters that his instructions to Cavan’s jockey, Pete Anderson, were “Every time Tim Tam made a move on us, Pete was to let Cavan out another notch.”

And as the pair of rivals rounded the far turn, Tim Tam moved to take the lead, with Cavan maintaining his lead as they moved past the other horses to become the frontrunners. There was a brief moment when the two were head and head, but as they entered the final stretch, it was obvious that something was wrong with Tim Tam.

The colt ran bravely, but he finished second in the Belmont Stakes–six lengths behind Cavan. Somewhere before the final stretch, Tim Tam had broken one of the sesamoid bones in his right foreleg.

Surprisingly, even with the injury, he managed to hobble across the wire more than five lengths ahead of Flamingo’s third-place finisher. Though he never raced again, Tim Tam went on to sire 14 stakes winners.

1944 — Pensive by Half a Length to Bounding Home


Pensive almost didn’t make it to the 1944 Kentucky Derby. Not because of procrastination, but rather because his trainer, Ben Jones, didn’t think he was of Kentucky Derby quality. But with 15 other horses entered, the slate looked wide open, and Pensive was added to the list.

In the Derby, Pensive laid back in the tall grass until the final stretch, where he moved in toward the rail and began whittling away at the lead of Broadcloth. Pensive’s efforts succeeded, and he finished the Derby as the winner by four-and-a-half lengths.

The Preakness was run the following week with a seven-horse field, and again Pensive trailed the frontrunners into the final stretch when he began jostling his way toward the front. He managed to slip into the lead, where he finished—3/4 of a length ahead of Platter, the second-place finisher.

Understandably, Pensive entered the Belmont Stakes starting gate as the favorite. And at the break, the race looked much like his previous two runs, with Pensive biding his time until the stretch.

But this time, he had some real competition—the 16/1 underdog Bounding Home began to close on him from the right, and when the dueling pair reached the wire. Bounding Home was ahead by half a length.

Incidentally, Pensive went on to sire the winner of the 1949 Kentucky Derby, Ponder. And Ponder sired Needles, winner of the 1956 Kentucky Derby.

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J.W. Paine

J.W. Paine is one of the most experienced writers at GamblingSites.com. He's written for television and the printed media, and is a published novelist (as Tom Elliott).

Paine loves writing about Las Vegas nearly as much he loves living here. An experienced gambler, he's especially familiar with thoroughbred horseracing, poker, blackjack, and slots.

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